DE286920C - - Google Patents
Info
- Publication number
- DE286920C DE286920C DENDAT286920D DE286920DA DE286920C DE 286920 C DE286920 C DE 286920C DE NDAT286920 D DENDAT286920 D DE NDAT286920D DE 286920D A DE286920D A DE 286920DA DE 286920 C DE286920 C DE 286920C
- Authority
- DE
- Germany
- Prior art keywords
- acetone
- alkali
- acetylene
- parts
- sodium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- 239000003513 alkali Substances 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 3
- GKHOLUJNLGYFHA-UHFFFAOYSA-N [Na].CC(C)=O Chemical compound [Na].CC(C)=O GKHOLUJNLGYFHA-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JQZGUQIEPRIDMR-UHFFFAOYSA-N 3-methylbut-1-yn-1-ol Chemical class CC(C)C#CO JQZGUQIEPRIDMR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Durch das Hauptpatent ist u. a. ein Verfahren zur Einführung der OxyisopropylgruppeThe main patent is, inter alia. a method of introducing the oxyisopropyl group
CH3:CH 3 :
CH1-C-CH 1 -C-
OHOH
in organische Verbindungen geschützt, welches darin besteht, daß man auf die Lösung von Natriumaceton in Äther, Ligroin usw. Kohlenwasserstoffe bei niedriger Temperatur einwirken läßt.protected in organic compounds, which consists in the fact that one on the solution of Sodium acetone in ether, ligroin, etc. hydrocarbons lets act at low temperature.
Gemäß dem Zusatzpatent 284764 läßt sich dieselbe Reaktion auch allgemein mit Alkaliaceton ausführen.According to the additional patent 284764, the same reaction can also generally be carried out with alkali acetone carry out.
Es wurde nun gefunden, daß es in vielen Fällen zweckmäßig ist, an Stelle von fertig gebildetem Acetonalkali Acetonalkali im Entstehungszustand anzuwenden. Gegenüber dem Verfahren des Hauptpatents bietet die Anwendung von nascierendem Acetonalkali den Vorzug, daß neben der Vereinfachung des technischen Verfahrens sich die Ausbeute an dem gewünschten Reaktionsprodukt erhöht und die Bildung von Kondensationsprodukten des Acetons ausbleibt, die sich sonst nicht ganz vermeiden läßt. Bei der den Gegenstand des vorliegenden Verfahrens bildenden Anwendung von Kohlenwasserstoffen ist die neue Arbeitsweise derjenigen des Hauptpatents auch darin überlegen, daß die Kühlung der Reaktionsflüssigkeit nicht durch Kältemischung zu erfolgen braucht, sondern daß hierfür Eis oder kaltes Wasser benutzt werden kann.It has now been found that in many cases it is convenient to use instead of done Acetone alkali formed Acetone alkali in the state of formation apply. Compared to the method of the main patent, the application of nascent acetone alkali offers the Advantage that, in addition to the simplification of the technical process, the yield increases the desired reaction product and the formation of condensation products of acetone does not occur, which otherwise cannot be completely avoided. When the subject of the present process forming application of hydrocarbons is the new one Operation is superior to that of the main patent in that the cooling of the reaction liquid does not need to be done by cold mixture, but that this ice or cold water can be used.
Kondensation von Natriumaceton mit Acetylen zu 3-MethylbutinolCondensation of sodium acetone with acetylene to form 3-methylbutynol
CH,CH,
CH,CH,
C=CH.C = CH.
OHOH
40 Teile fein zerriebenes Natriumamid werden mit 500 Teilen absolutem Äther überschichtet. Die mit Eis gekühlte Mischung wird mit trockenem Acetylengas gesättigt und darauf unter Rühren in langsamem Strome Acetylen eingeleitet, das mit Aceton im richtigen Verhältnis beladen ist. Um dies zu erreichen, läßt, man das Acetylen eine Waschflasche passieren, die mit 58 Teilen Aceton beschickt ist und in einem auf 30 ° erwärmten Bade steht. So wird erreicht, daß das Aceton ganz allmählich mit dem Natriumamid in Berührung kommt und das Acetonnatrium in dem Maße, als es entsteht, sofort vom Acetylen gebunden wird. Sobald alles Aceton verschwunden ist, wird die farblose Reaktionslösung weiter verarbeitet, wie in dem40 parts of finely ground sodium amide are covered with a layer of 500 parts of absolute ether. The ice-cooled mixture is saturated with dry acetylene gas and then slowly stirred while stirring Introduced streams of acetylene, which is loaded with acetone in the correct ratio. To this To achieve, the acetylene is allowed to pass through a wash bottle containing 58 parts Acetone is charged and is in a bath heated to 30 °. So it is achieved that the acetone gradually comes into contact with the sodium amide and the acetone sodium to the extent that it is formed, is immediately bound by the acetylene. Once all of the acetone is gone, the one becomes colorless Reaction solution further processed as in that
Hauptpatent angegeben ist. Das so gewonnene 3-Methylbutinol ist ein farbloses, mit
Wasser in jedem Verhältnis mischbares öl, das bei 102 bis 103° siedet.
Zu nahezu dem gleichen Resultat gelangt man, wenn man in dem vorliegenden Beispiel
an Stelle der 40 Teile Natriumamid 25 Teile metallisches Natrium oder 40 Teile metallisches
Kalium, in Scheiben geschnitten, verwendet.Main patent is indicated. The 3-methylbutynol obtained in this way is a colorless oil which can be mixed with water in any ratio and boils at 102 to 103 °.
Almost the same result is obtained if, in the present example, instead of 40 parts of sodium amide, 25 parts of metallic sodium or 40 parts of metallic potassium, sliced, are used.
Ebenso wie das Natriumamid gehen auch die genannten Metalle beim Einleiten des mit Acetondampf beladenen Acetylens allmählich in Lösung. Die Verarbeitung der Reaktionslösung erfolgt hier zweckmäßig in der Weise, daß man Eiswasser hinzufügt, das freie Alkali durch Kohlensäure absättigt und die ätherische Schicht über Kaliumkarbonat trocknet.Just like the sodium amide, the metals mentioned also go along with the introduction of the Acetone vapor laden acetylene gradually dissolves. The processing of the reaction solution is expediently carried out here in the manner that one adds ice water, saturates the free alkali with carbonic acid and the ethereal Layer dries over potassium carbonate.
Das nach dem Abdestillieren des Äthers an der Kolonne zurückbleibende 3-Methylbutinol siedet bei 95 bis 103°. Die etwas niedrigere Siedetemperatur ist durch Beimischung von hydriertem 3-Methylbutinol bedingt, das sich durch oft wiederholte, fraktionierte Destillation beseitigen läßt.The 3-methylbutynol remaining on the column after the ether has been distilled off boils at 95 to 103 °. The slightly lower boiling point is due to the addition of hydrogenated 3-methylbutynol, which is often repeated, fractional distillation can eliminate.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE286920C true DE286920C (en) | 1900-01-01 |
Family
ID=542189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT286920D Expired DE286920C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE286920C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE740988C (en) * | 1938-01-21 | 1943-11-02 | Ig Farbenindustrie Ag | Process for the preparation of alcohols of the acetylene series |
-
0
- DE DENDAT286920D patent/DE286920C/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE740988C (en) * | 1938-01-21 | 1943-11-02 | Ig Farbenindustrie Ag | Process for the preparation of alcohols of the acetylene series |
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